EP3985004A1 - Agent chimique agricole et horticole dont l'ingrédient actif est un nouveau dérivé d'imidazopyridine-2-carboxamide - Google Patents

Agent chimique agricole et horticole dont l'ingrédient actif est un nouveau dérivé d'imidazopyridine-2-carboxamide Download PDF

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Publication number
EP3985004A1
EP3985004A1 EP20822844.5A EP20822844A EP3985004A1 EP 3985004 A1 EP3985004 A1 EP 3985004A1 EP 20822844 A EP20822844 A EP 20822844A EP 3985004 A1 EP3985004 A1 EP 3985004A1
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EP
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Prior art keywords
group
imidazopyridine
compound
sup
agricultural
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EP20822844.5A
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German (de)
English (en)
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EP3985004A4 (fr
Inventor
Katsuaki Oyama
Kohei OJIMA
Koichi Araki
Saki MORISHITA
Toshiki Fukuchi
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Agro Kanesho Co Ltd
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Agro Kanesho Co Ltd
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Publication of EP3985004A1 publication Critical patent/EP3985004A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G7/00—Botany in general
    • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to a new imidazopyridine-2-carboxamide compound and a method of using the compound as an active ingredient of an agricultural and horticultural chemical agent, in particular, as an agricultural and horticultural insecticide.
  • imidazopyridine-2-carboxamide derivatives that are similar to the present invention, the following compounds A and B are disclosed.
  • Patent Literature 1 discloses compounds including the following compound A. However, Patent Literature 1 does not disclose any N-alkyloxy group and any N-alkylthio group, which groups are possessed by the present invention compound at all.
  • Patent Literature 1 Compound A
  • Patent Literature 2 discloses compounds including the following compound B, but the acid site thereof is limited to a pyridine ring, and Patent Literature 2 does not disclose any imidazopyridine ring at all.
  • Patent Literature 2 Compound B
  • the present inventors diligently studied and, as a result, found that the present compound has a significantly high insecticidal activity compared to the compounds A and B. Such an improvement in the activity was completely unexpected and was first revealed by the experiments carried out by the present inventors.
  • Patent Literatures encompassing the following compounds as carboxamide derivatives having an acid site of an aromatic ring or an aromatic heterocyclic ring and including an N-alkyl group have been disclosed.
  • Patent Literature 3 Patent Literature 4
  • Patent Literature 5 Patent Literature 6
  • Patent Literature 7 Patent Literature 7
  • these compounds are not compounds having an N-alkoxy group or an N-alkylthio group.
  • the acid side portion also does not include an imidazopyridine ring.
  • the present invention is to provide a new substance useful for controlling various pests in the field of agriculture and horticulture.
  • the present invention is to provide a substance which exhibits a high controlling effect also on various pests having resistance to conventional insect pest control agents; which further exhibits the effect with a low dose; and which has a high safety with reduced problems of residual toxicity and environmental problems such as environmental pollution.
  • an imidazopyridine-2-carboxamide derivative represented by the following formula (1) which is a new compound which was not described in the literatures, is useful as agricultural and horticultural chemical agents which can meet the above demands, in particular, which are useful as agricultural and horticultural insecticides, and thus the present invention has been accomplished.
  • the present invention relates to an imidazopyridine-2-carboxamide derivative represented by the following formula (1): [in the formula,
  • the compound of the present invention exhibits an excellent effect as an agricultural and horticultural chemical agent, in particular, as an agricultural and horticultural insecticide.
  • the present compound provides an effect on pests that parasitize pet animals, such as dogs and cats, or livestock, such as cows and sheep.
  • halogen atom represents a chlorine atom, a bromine atom, a iodine atom, or a fluorine atom
  • C 1-6 alkyl group represents a linear or branched chain alkyl group having 1 to 6, preferably 1 to 3 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, and an isohexyl group
  • C 1-6 haloalkyl group represents the above prescribed linear or branched chain alkyl
  • C 1-6 haloalkyl group examples include the above prescribed linear or branched chain alkyl groups having 1 to 6 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms, such as a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2-iodoethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group, a 1-fluoroisopropyl group, a 3-fluoropropyl group, a fluoromethyl
  • C 1-6 alkoxy group examples include linear or branched chain alkoxy groups having 1 to 6, preferably 1 to 3 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group, and an n-hexyloxy group.
  • C 1-6 haloalkoxy group examples include the above prescribed linear or branched chain alkoxy groups having 1 to 6 carbon atoms substituted with 1 to 9 halogen atoms, such as a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, a 1-fluoroethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2-iodoethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,2-trichloroethoxy group, a pentafluoroethoxy group, a 1-fluoroisopropoxy group, a 3-fluoropropoxy
  • C 3-6 alkenyloxy group examples include linear or branched chain alkenyloxy groups having 3 to 6, preferably 3 to 5 carbon atoms and having at least one double bond at an arbitrary position, such as an allyloxy group, an isopropenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 1-methyl-2-propenyloxy group, a 2-pentenyloxy group, a 3-pentenyloxy group, a 4-pentenyloxy group, a 1,1-dimethyl-2-propenyloxy group, a 1-ethyl-2-propenyloxy group, a 1-methyl-2-butenyloxy group, a 1-methyl-3-butenyloxy group, a 2-hexenyloxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 5-hexenyloxy group, a 1,1-dimethyl-2-butenyloxy group
  • C 3-6 haloalkenyloxy group examples include the above prescribed linear or branched chain alkenyloxy groups having 3 to 6 carbon atoms, having at least one double bond at an arbitrary position and further being substituted with 1 to 13, preferably 1 to 7 halogen atoms, such as a 3-chloro-2-propenyloxy group, a 3,3-difluoro-2-allyloxy group, a 3,3-dichloro-2-allyloxy group, a 4,4,4-trifluoro-2-butenyloxy group, a 4,4,4-trifluoro-3-butenyloxy group, a 5-chloro-3-pentenyloxy group, and a 6-fluoro-2-hexenyloxy group.
  • halogen atoms such as a 3-chloro-2-propenyloxy group, a 3,3-difluoro-2-allyloxy group, a 3,3-dichloro-2-allyloxy group, a 4,4,4-
  • C 3-6 alkynyloxy group examples include linear or branched chain alkynyloxy groups having 3 to 6, preferably 3 to 5 carbon atoms and having at least one triple bond at an arbitrary position, such as a 2-propynyloxy group, a 1-methyl-2-propynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 1-butynyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 1-pentynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, a 4-pentynyloxy group, a 1-methyl-2-butynyloxy group, a 1-methyl-3-butynyloxy group, a 1,1-dimethyl-2-butynyloxy group, a 1,1-dimethyl-3-butynyloxy group, a 1-methyl-3-penty
  • C 3-6 haloalkynyloxy group examples include the above prescribed linear or branched chain alkynyloxy groups having 3 to 6 carbon atoms, having at least one triple bond at an arbitrary position and being substituted with 1 to 9, preferably 1 to 6 halogen atoms, such as a 4,4,4-trifluoro-2-butynyloxy group, a 5,5,5-trifluoro-3-pentynyloxy group, a 1-methyl-3,3,3-trifluoro-2-butynyloxy group, and a 1-methyl-5,5,5-trifluoro-2-pentynyloxy group.
  • C 1-6 alkylthio group examples include linear or branched chain alkylthio groups having 1 to 6, preferably 1 to 3 carbon atoms, such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, a sec-butylthio group, a tert-butylthio group, an n-pentylthio group, and an n-hexylthio group.
  • C 1-6 alkylsulfinyl group examples include linear or branched chain alkylsulfinyl groups having 1 to 6, preferably 1 to 3 carbon atoms, such as a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an isopropylsulfinyl group, an n-butylsulfinyl group, a sec-butylsulfinyl group, a tert-butylsulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.
  • C 1-6 alkylsulfonyl group examples include linear or branched chain alkylsulfonyl groups having 1 to 6, preferably 1 to 3 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.
  • C 1-6 haloalkylthio group examples include linear or branched chain alkylthio groups having 1 to 6, preferably 1 to 3 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms, such as a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group, a 1-fluoroethylthio group, a 2-fluoroethylthio group, a 2,2-difluoroethylthio group, a 2,2,2-trifluoroethylthio group, a 2-chloro-2,2-difluoroethylthio group, a 1-chloroethylthio group, a 2-chlor
  • C 1-6 haloalkylsulfinyl group examples include linear or branched chain alkylsulfinyl groups having 1 to 6, preferably 1 to 3 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms, such as a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a dichloromethylsulfinyl group, a trichloromethylsulfinyl group, a monobromomethylsulfinyl group, a dibromomethylsulfinyl group, a tribromomethylsulfinyl group, a 1-fluoroethylsulfinyl group, a 2-fluoroethylsulfinyl group, a 2,2-difluoroethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group,
  • C 1-6 haloalkylsulfonyl group examples include linear or branched chain alkylsulfonyl groups having 1 to 6, preferably 1 to 3, carbon atoms substituted with 1 to 13, preferably 1 to 9, halogen atoms, such as a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, a tribromomethylsulfonyl group, a 1-fluoroethylsulfonyl group, a 2-fluoroethylsulfonyl group, a 2,2-difluoroethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group,
  • Examples of the salt of the imidazopyridine-2-carboxamide derivative represented by the formula (1) of the present invention include inorganic acid salts, such as hydrochloride, sulfate, nitrate, and phosphate, and organic acid salts, such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
  • inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate
  • organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
  • the imidazopyridine-2-carboxamide derivative represented by the formula (1) of the present invention may include one or more asymmetric centers in its structural formula, and two or more optical isomers and diastereomers may be present.
  • the present invention encompasses these optical isomers and a mixture containing them in any arbitrary proportions.
  • two geometrical isomers derived from a carbon-carbon double bond may be present, and the present invention encompasses these geometrical isomers and a mixture containing them in any arbitrary proportions.
  • R 2 is a C 1-3 alkyl group or a C 1-3 haloalkyl group
  • R 2 is a methyl group
  • R 1 is a C 1-3 alkyl group or a C 1-3 haloalkyl group
  • R 1 is a C 1-3 alkyl group
  • R 3 and R 4 are C 1-3 haloalkyl groups
  • R 3 and R 4 are C 1-3 alkyl groups
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 , A 5 , X, and m are as defined above].
  • the imidazopyridine-2-carboxamide derivatives (1-1) and (1-2) represented by the formula (1) are manufactured by oxidation reaction of the imidazopyridine-2-carboxamide derivative represented by the formula (1-0).
  • a solvent which is inert to the reaction can be widely used, and examples thereof include aliphatic or alicyclic hydrocarbon solvents, such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents, such as benzene, chlorobenzene, toluene, and xylene; halogenated hydrocarbon solvents, such as methylene chloride, 1,2-dichloroethane, and chloroform; alcoholic solvents, such as methanol and ethanol; ester solvents, such as methyl acetate and ethyl acetate; ketone solvents, such as acetone and methyl ethyl ketone; amide solvents, such as N,N-dimethylformamide; nitrile solvents, such as acetonitrile and propionitrile; non-protonic polar solvents, such as N-methylpyrrol
  • the oxidizing agent to be used in the oxidation reaction of the formula (1-0) is, for example, m-chloroperbenzoic acid, sodium periodate, or hydrogen peroxide.
  • Such an oxidizing agent can be usually used in an amount of 1 to 3 equivalents, preferably 1 to 2.5 equivalents, with respect to the imidazopyridine-2-carboxamide derivative represented by the formula (1-0).
  • the reaction can be performed usually within a temperature range of -78°C to the boiling point of the used solvent, and the reaction is preferably performed at a temperature from 0°C to room temperature.
  • the reaction time varies depending on the reaction temperature, etc., and although it cannot be said unconditionally, the reaction is usually completed in about 0.5 to 24 hours.
  • the target compounds obtained by each of the above reactions can be easily isolated from a reaction mixture by an isolation method that is generally performed, such as organic solvent extraction, chromatography, a recrystallization method, or a distillation method and can be further purified by a general purification method.
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 , A 5 , X, and m are as defined above, and Y represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, or a trifluoromethanesulfonyloxy group].
  • an imidazopyridine-2-carboxamide derivative represented by the formula (1-3) and a halogenated ether derivative or a halogenated thioether derivative represented by YCH 2 XR 2 are allowed to react with each other in a solvent in the presence of a base according to the method described in Bioorganic Medicinal Chemistry Letters, 18 (20), 5537-5540 (2008 ) to manufacture a compound of the formula (1-0).
  • a known solvent can be widely used as long as the solvent is inert to the reaction, and examples thereof can include ether solvents, such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; amide solvents, such as N,N-dimethylformamide; and solvents, such as dimethyl sulfoxide, N-methylpyrrolidone, and N,N'-dimethylimidazolinone. These solvents can be used alone or as a mixture of two or more thereof as needed.
  • ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane
  • amide solvents such as N,N-dimethylformamide
  • solvents such as dimethyl sulfoxide, N-methylpyrrolidone, and N,N'-dimethylimidazolinone.
  • a known inorganic base or organic base can be used, and examples thereof can include alkali metal hydrides, such as sodium hydride and potassium hydride; alkali metal carbonates, such as sodium carbonate and potassium carbonate; alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; alkali metal alkoxides, such as potassium t-butoxide; and organic bases, such as triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4-(N,N-dimethylamino)pyridine, N,N-dimethylaniline, N,N-diethylaniline, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane (DABCO), and 1,8-diazabicyclo[5.4.0]-7-undecene
  • alkali metal hydrides
  • the amount of the base used can be usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, based on 1 mole of the compound of the formula (1-3).
  • the reaction is preferably performed at a temperature from 0°C to the boiling point of the used solvent, more preferably at a temperature from 0°C to 80°C.
  • the reaction is usually completed in a reaction time of about 0.5 to 24 hours.
  • the object compound is isolated from the reaction system containing the object compound by a usual method and the object compound can be purified by, for example, recrystallization or column chromatography as needed, so as to produce the object compound.
  • the object compound can be manufactured.
  • the object can be subjected to the subsequent process without isolating the object compound from the reaction system.
  • the imidazopyridine-2-carboxamide derivative represented by the general formula (1-3) to be used in the present reaction can be synthesized, for example, according to the method described in JP-A-2018-24672 .
  • the physical properties in the table show the nature or the melting point (°C), "n” represents normal, “i” represents iso, “Me” represents a methyl group, “Et” represents an ethyl group, and “Pr” represents a propyl group.
  • the compound of the present invention can be used for prevention and extermination of organisms that are harmful in agriculture or indoors or in the forest, to livestock, or in various situations such as hygiene. Specific usage situations, target harmful organisms, and usage methods will now be shown, but the contents of the present invention are not limited thereto.
  • the compound of the present invention represented by the formula (1) can also be used for controlling harmful organisms, such as arthropods, mollusks, nematodes, and fungi and bacteria including Eumycota, Myxomycota, Bacteriomycota, and Actinomycota, that damage crops, for example, food crops (e.g., rice, wheat varieties such as barley, wheat, rye, and oats, corn, potato, sweet potato, taro, and beans such as soybeans, adzuki beans, broad beans, peas, common beans, and peanuts), vegetables (e.g., Brassicaceae crops such as cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, and Japanese mustard spinach, cucurbitaceous fruits such as pumpkin, cucumber, watermelon, oriental melon, and melon, eggplant, tomato, bell pepper, pepper, okra, spinach, lettuce, lotus root, carrot, burdock, and alliaceous plants such as garlic, onion, and green onion), mushrooms
  • Noctuidae such as Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni, Mamestra brassicae, Spodoptera exigua, and Spodoptera litura
  • Yponomeutidae such as Plutella xylostella
  • Tortricidae such as Adoxophyes orana fasciata, Adoxophyes honmai, Archips fuscocupreanus, Homona magnanima, Caloptilia theivora, and Grapholita molesta
  • Psychidae such as Eumeta minuscula
  • Lyonetiidae such as Lyonetia prunifoliella malinella and Lyonetia clerkella
  • Phyllocnistinae such as
  • Examples of the disease to which the compound of the present invention represented by the formula (1) can be applied include rice diseases, such as blast disease (Pyricularia oryzae), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bacterial palea browning (Pantoea ananatis), brown stripe disease (Acidovorax avene subsp. avenae), sheath brown rot (Pseudomonas fuscovaginae), bacterial leaf blight (Xanthomonas oryzae pv.
  • rice diseases such as blast disease (Pyricularia oryzae), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bacterial palea browning (Pantoea ananatis), brown stripe disease (Acidovorax avene subsp. avenae), sheath brown
  • wheat diseases such as powdery mildew (Erysiphe graminis), red mildew (Gibberella zeae), leaf rust (Puccinia striiformis, P. graminis, P. recondita, and P. hordei), snow mold (Typhula sp. and Micronectriella nivalis), loose kernel smut (Ustilago tritici and U.
  • wheat diseases such as powdery mildew (Erysiphe graminis), red mildew (Gibberella zeae), leaf rust (Puccinia striiformis, P. graminis, P. recondita, and P. hordei), snow mold (Typhula sp. and Micronectriella nivalis), loose kernel smut (Ustilago tritici and U.
  • citrus fruit diseases such as black spot (Diaporthe citri), spot anthracnose (Elsinoe fawcetti), fruit rot (Penicillium digitatum and P. italicum), brown rot (Phytophthora citrophthora and P.
  • nicotianae nicotianae
  • scab Physically scab
  • apple diseases such as Molinia leaf blight (Monilinia mali), valsa canker (Valsa mali), powdery mildew (Podosphaera leucotricha), alternaria leaf spot (Alternaria mali), scab (Venturia inaequalis), black spot (Mycospherella pomi), bitter rot (Colletotrichum acutatum), ring rot (Botryosphaeria berengeriana), rust (Gymnosporangium yamadae), and brown rot (Monilinia fructicola);
  • the compound of the present invention represented by the formula (1) can also be used for controlling arthropods and fungi that are active indoors in buildings, including ordinary houses, that perpetrate or rot wood and its processed wooden furniture, stored food, clothes, books, etc., and that damage our lives.
  • Specific examples of the harmful organisms include the followings.
  • Phinotermitidae such as Coptotermes formosanus, Reticulitermes speratus, other termites of Reticulitermes spp. (e.g., Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, and R. santonensis), and Incisitermes minor;
  • Termitidae such as Odontotermes formosanus;
  • Termopsidae such as Hodotermopsis jzponica;
  • Kalotermitidae such as Cryptotermes domesticus
  • the compound of the present invention represented by the formula (1) can also be used for controlling harmful organisms that are injurious to trees in natural forests, planted forests, and urban green spaces or that weaken the trees.
  • Specific examples of the harmful organisms include the followings.
  • Lymantriidae such as Calliteara argentata, Euproctis pseudoconspersa, Orygiaction approximans, Euproctis subflava, and Lymantria dispar
  • Lasiocampidae such as Malacosoma neustria testacea, Dendrolimus spectabilis, and Dendrolimus superans
  • Pyralidae such as Crytoblabes loxiella
  • Noctuidae such as Agrotis segetum
  • Tortricidae such as Ptycholoma lecheana circumclusana, Cydia kurokoi, and Cydia cryptomeriae
  • Arctiidae such as Spilosoma imparilis and Hyphantria cunea
  • Nepticulidae such as Stigmella castanopsi
  • the compound of the present invention represented by the formula (1) can also be used for preventing, treating, or controlling arthropods, nematodes, trematodes, cestodes, and protozoans that internally or externally parasitize livestock and pets, i.e., vertebrates, especially warm-blooded vertebrates, such as cows, sheep, goats, horses, pigs, fowls, dogs, cats, and fish.
  • livestock and pets i.e., vertebrates, especially warm-blooded vertebrates, such as cows, sheep, goats, horses, pigs, fowls, dogs, cats, and fish.
  • target animal species include, in addition to the above, pets and experimental animals, e.g., rodents, such as mice, rats, hamsters, and squirrels; carnivorous animals, such as ferrets; and birds, such as ducks and pigeons.
  • specific examples of the harmful organisms include the followings.
  • Tabanidae such as Tabanus rufidens and Tabanus chrysurus
  • Muscidae such as Musca bezzii, Musca domestica, and Stomoxys calcitrans
  • Gasterophilidae such as Gasterophilus intestinalis
  • Hypodermatidaed such as Hypoderma bovis
  • Oestridae such as Oestrus ovis
  • Calliphoridae such as Aldrichina graham
  • Phoridae such as Megaselia spiracularis
  • Sepsidae such as Sepsis punctum
  • Psychodidae such as Telmatoscopus albipunctatus and Psychoda alternata
  • Culicidae such as Culex pipiens molestus, Culex pipiens pallens, Anopheles sinensis, Culex pipiens tri
  • the compound of the present invention represented by the formula (1) can also be used for exterminating harmful organisms that cause direct harm or discomfort to the human body or for maintaining public health against harmful organisms that carry and transmit pathogens.
  • Specific examples of the harmful organisms include the followings.
  • Lymantriidae such as Sphrageidus similis
  • Lasiocampidae such as Kunugia undans
  • Limacodidae such as Parasa consocia
  • Zygaenidae such as Artona martini
  • the compound of the present invention represented by the formula (1) is particularly valuable, in controlling harmful organisms that damage crops, trees in natural forests, planted forests, and urban green spaces, and ornamental plants, such as arthropods, gastropods, nematodes, and fungi.
  • the compound of the present invention can also be present in a commercially useful formulation and a use form prepared from such a formulation as a mixed agent with another active compound such as an insecticide, a miticide, a nematicide, a fungicide, a synergist, a plant growth regulator, a poison bait, or an herbicide.
  • the use form can be, for example, a water dispersible powder, a granular water dispersible powder, a dry flowable agent, a water-soluble agent, an emulsion agent, a liquid agent, an oil agent, a flowable agent such as a suspension agent in water or an emulsion agent in water, capsules, a powder formulation, granules, fine granules, a bait, tablets, a spray formulation, a haze formulation, or an aerosol formulation.
  • various pesticidal adjuvants that have been conventionally used in the technical field of agricultural and horticultural chemical agent can be appropriately used. These pesticidal adjuvants can be used for the purpose of, for example, improvement of the effect, stabilization, and improvement of the dispersibility of agricultural and horticultural chemical agents.
  • the pesticidal adjuvant examples include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersant, and a disintegrant.
  • the liquid carrier include water; aromatic hydrocarbons, such as toluene and xylene; alcohols, such as methanol, butanol, and glycol; ketones, such as acetone; amides, such as dimethylformamide; sulfoxides, such as dimethyl sulfoxide; and methylnaphthalene, cyclohexane, animal and vegetable oils, and fatty acid.
  • solid carrier examples include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, and gum Arabic.
  • emulsifier or the dispersant ordinary surfactants can be used.
  • an anionic surfactant, a cationic surfactant, a nonionic surfactant, or an amphoteric surfactant, such as higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine can be used.
  • a spreading agent for example, a spreading agent; a wetting agent, such as dialkyl sulfosuccinate; a sticking agent, such as carboxymethyl cellulose or polyvinyl alcohol; and a disintegrant, such as sodium lignin sulfonate or sodium lauryl sulfate can be used.
  • a wetting agent such as dialkyl sulfosuccinate
  • a sticking agent such as carboxymethyl cellulose or polyvinyl alcohol
  • a disintegrant such as sodium lignin sulfonate or sodium lauryl sulfate
  • One of the compounds of the present invention may be used alone as an active ingredient, or a combination of two or more thereof may be used as an active ingredient.
  • the content of the compound of the present invention as the active ingredient is, for example, 0.01 to 99.5 mass% and is preferably selected from a range of 0.5 to 90 mass% and may be appropriately determined according to various conditions such as formulation form and application method.
  • a powder formulation so as to contain about 0.5 to 20 mass%, preferably 1 to 10 mass%, of the active ingredient, a water dispersible powder so as to contain about 1 to 90 mass%, preferably 10 to 80 mass%, of the active ingredient, and an emulsion agent so as to contain about 1 to 90 mass%, preferably 10 to 40 mass%, of the active ingredient.
  • the formulation can be used by spraying to leaves and stems of plants in a place where the damage caused by these harmful organisms is occurring or can occur or by being allowed to be absorbed from roots by treating soil or the like through, for example, soil all layer mixing, plating row application, bed soil mixing, cell seedling, planting hole treatment, plant root treatment, top dressing, rice plant box treatment, or submerged application.
  • the formulation can be used by seed treatment, such as soaking of seeds in chemicals, seed powder coating, or calper treatment, application to nourishing solution in nutriculture (hydroponic culture), or smoking or trunk injection.
  • a water dispersible powder, a granular water dispersible powder, a dry flowable agent, a water soluble agent, an emulsion agent, a liquid agent, a flowable agent such as a suspension agent in water or an emulsion agent in water, or capsules is diluted with water and, while it varies depending on the type, cultivation form, or growing condition of the target plant, in general, the diluted formulation may be sprayed to a crop or the like in an application amount of 10 to 1000 L per 10 ares.
  • a powder formulation, a spray formulation, or an aerosol formulation, a crop or the like may be treated with the formulation as its state.
  • Examples of the application method when the target harmful organisms mainly harm plants in the soil or when the target harmful organisms are controlled by allowing a chemical agent to be absorbed from the roots include a method of applying a formulation to the plant root or nursery bed for raising seedling with or without dilution in water, a method of spraying granules to the plant root or the nursery bed for seedling, a method of spraying a powder formulation, a water dispersible powder, a granular water dispersible powder, or granules to mix them with the whole soil before sowing or transplanting, and a method of spraying a powder formulation, a water dispersible powder, a granular water dispersible powder, granules, or fine granules to the planting holes or planting rows before sowing or planting plants.
  • a water dispersible powder, a granular water dispersible powder, a water-soluble agent, an emulsion agent, a liquid agent, a flowable agent such as a suspension agent in water or an emulsion agent in water, or capsules is diluted with water and may be sprayed to the soil surface or irrigated into soil, in general, in an application amount of 5 to 500 L per 10 ares, so as be uniform in the entire treatment area.
  • a powder formulation, granules, fine granules, or a bait may be sprayed to the soil surface in the state of the formulation so as be uniform in the entire treatment area.
  • the spraying or irrigation may be performed around the seeds, crops, or trees to be protected from harm.
  • the active ingredient may be mechanically dispersed by plowing during spraying or after spraying.
  • a dosage form such as a powder formulation, a granular water dispersible powder, granules, or fine granules.
  • Application can be also performed by mixing the formulation with culture soil, and culture soil may be mixed with a powder formulation, a granular water dispersible powder, granules, or fine granules by, for example, bed soil mixing, cover soil mixing, or mixing with the entire culture soil.
  • culture soil and a formulation may be alternately applied in a layer form.
  • a solid formulation such as a jumbo agent, a pack agent, granules, or a granular water dispersible powder or a liquid agent such as a flowable agent or an emulsion agent is sprayed to a paddy field in a submerged condition.
  • an appropriate formulation can also be sprayed to or injected in soil directly or as a mixture with a fertilizer.
  • a liquid chemical agent such as an emulsion agent or a flowable agent, at a source of water inflow to a paddy field, such as a water outlet or irrigation equipment allows application with the supply of water in a labor-saving manner.
  • Examples of the method of seed treatment include a method of immersing seeds in a liquid or solid formulation in a liquid state with or without diluting to allow the chemical to attach to or infiltrate into the seeds, a method of mixing a solid formulation or a liquid formulation with seeds for dressing treatment to allow the formulation to adhere to the surfaces of the seeds, a method of mixing seeds with an adhesive carrier, such as a resin or a polymer, to coat the seeds with the carrier, and a method of spraying a formulation near seeds at the same time as planting.
  • an adhesive carrier such as a resin or a polymer
  • seeds to be subjected to seed treatment means early cultivated plant bodies used for plant propagation, and examples thereof include, in addition to seeds, bulbs, tubers, seed potatoes, shoots, propagules, and vegetative propagation plants for bulb or cutting cultivation.
  • soil or “cultivation carrier” for a plant in application indicates a support for cultivating a crop, in particular, a support for allowing roots to grow, and the material thereof is not particularly limited as long as it allows plants to grow.
  • the support may be so-called soil, nursery mat, or water, and the examples of the material include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substance, polymer substance, rock wool, glass wool, wood chips, and bark.
  • Treatment of a cultivated plant to be transplanted in sowing and raising of seeding period is preferably direct treatment of seeds or irrigation treatment of a chemical agent in a liquid state or spraying treatment of granules to a nursery bed.
  • treatment of planting holes with granules at the time of planting or mixing granules with the cultivation carrier near the transplantation position is also preferable.
  • the compound of the present invention represented by the formula (1) is also valuable for protecting wood (standing trees, fallen trees, processed timber, stored timber, or structural timber) from harm of insects, such as termites and beetles, and fungi.
  • the controlling is possible by a method of performing spraying, injection, irrigation, or application of an oil agent, an emulsion agent, a water dispersible powder, a sol formulation or spraying of a powder formulation or granules to the wood or the soil around the wood.
  • the oil agent, the emulsion agent, the water dispersible powder, or the powder formulation that is used in this situation can be present as a mixed agent with another active compound, such as an insecticide, a miticide, a nematicide, a fungicide, a repellent, or a synergist, and the total amount of active ingredient compounds in such a formulation is 0.0001 to 95 mass%.
  • the amount is preferably 0.005 to 10 mass%
  • the emulsion agent, the water dispersible powder, or the sol formulation the amount is preferably 0.01 to 50 mass%. In cases of controlling arthropods or fungi, 0.01 to 100 g of the active ingredient compound is sprayed per 1 m 2 of soil or wood surface.
  • the compound of the present invention represented by the formula (1) can be used for protecting products of, for example, cereals, fruits, nuts, spices, and tobacco when they are stored as they are, in powdered forms, or in mixed states in products, from harm by Lepidoptera, Coleoptera, mites, and fungi.
  • animal products leather, fur, wool, feather, etc.
  • plant products cotton, paper, etc.
  • controlling is possible by a method of spraying an oil agent, an emulsion agent, a water dispersible powder, or a powder formulation, installing a resin transpiration agent, treating with a smoking agent or a haze formulation, installing granules, tablets, or a poison bait, or spraying aerosol.
  • These formulations can also be present as a mixed agent with another active compound, such as an insecticide, a miticide, a nematicide, a fungicide, a repellent, or a synergist, and the total amount of the active ingredient compounds in such a formulation can be 0.0001 to 95 mass%.
  • the compound of the present invention represented by the formula (1) is valuable for exterminating or preventing arthropods or fungi that parasitize the body surface of humans and livestock and cause direct harm such as skin feeding or blood sucking; arthropods, nematodes, trematodes, cestodes, or protozoans that spread human and livestock diseases or are mediators of such diseases; and arthropods that make humans uncomfortable.
  • the compound of the present invention can be orally administered as a meal or feed containing a small amount of the compound of the present invention or as an appropriate ingestible pharmaceutical chemical composition, for example, tablets, pills, capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated baits, or controlled release large pills including a pharmaceutically acceptable carrier or coating material, or another controlled release device to be retained in the gastrointestinal tract, or can be percutaneously administered as spray, powder, grease, cream, ointment, emulsion, lotion, a spot-on agent, a pore-on agent, or shampoo.
  • an appropriate ingestible pharmaceutical chemical composition for example, tablets, pills, capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated baits, or controlled release large pills including a pharmaceutically acceptable carrier or coating material, or another controlled release device to be retained in the gastrointestinal tract, or can be percutaneously administered as spray, powder, grease, cream, ointment, emulsion, lotion
  • the formulation generally contains 0.0001 to 0.1 mass%, preferably 0.001 to 0.01 mass%, of an active ingredient compound.
  • a device for example, a collar, medallion, or ear tag
  • the method for percutaneous administration or topical administration a device (for example, a collar, medallion, or ear tag) attached to an animal can be used for controlling arthropods locally or systemically.
  • the beverage When the compound is orally administered as a medicated drinking water, the beverage is usually a solution, suspension, or dispersion of the compound in an appropriate nontoxic solvent or water together with a suspension agent, such as bentonite, or a humectant or another excipient.
  • a beverage also contains an antifoam agent.
  • a beverage formulation generally contains 0.01 to 1.0 mass%, preferably 0.01 to 0.1 mass%, of an active ingredient compound.
  • capsules, pills, or tablets containing a predetermined amount of an active ingredient are used.
  • These use forms are manufactured by mixing an active ingredient with an appropriately finely crushed diluent, filler, disintegrant, and/or binder, such as starch, lactose, talc, magnesium stearate, or vegetable rubber.
  • a unit use prescription can widely change the mass and content of an insecticide according to the type of the host animal to be treated, the degree of infection, the type of the parasite, and the weight of the host.
  • the active compound in administration through animal feed, can be used by being homogeneously dispersed in the feed, as top dressing, or in a form of pellet.
  • the final content of the active ingredient compound in feed is 0.0001 to 0.05 mass% and preferably 0.0005 to 0.01 mass%.
  • the active compound to be dissolved or dispersed in a liquid carrier excipient can be parenterally administered to an animal by intragastric, intramuscular, intratracheal, or subcutaneous injection.
  • the active compound is suitably mixed with appropriate vegetable oil, such as peanut oil or cottonseed oil.
  • the content of the active ingredient compound is 0.05 to 50 mass% and preferably 0.1 to 5.0 mass%.
  • the active compound can be topically administered by mixing it with an appropriate carrier, such as dimethyl sulfoxide or a hydrocarbon solvent.
  • an appropriate carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is directly applied to the animal outer surface by spray or direct addition.
  • the compound of the present invention represented by the formula (1) can also be used as an insecticide against arthropods that cause direct harm or arthropods that are mediators of disease, by spraying, injecting, irrigating, or applying an oil agent, an emulsion agent, a water dispersible powder, etc., by spraying a powder formulation, etc., by treatment with a fumigant, a heat haze formulation such as a mosquito coil, self-burning smoking agent, or a chemical reaction-type haze formulation, a smoking agent such as fogging, or a ULV agent, or by installation of granules, tablets, or a poison bait in the surrounding environment where the harmful organisms may be latent, or by addition by dropping a floating powder formulation, granules, etc.
  • Lymantriidae which is also an agricultural and forest pest, can be controlled by the same method as above.
  • a method of mixing the compound with feed of livestock so that the compound is mixed with feces is effective, and against Culicidae, a method of volatilizing the compound in the air with an electric mosquito-repellent device or the like is also effective.
  • the formulations in these use forms can be present as mixed agents with another active compound, such as a pest control agent, a mite control agent, a nematode control agent, a disease control agent, a repellent, or a synergist, and the total amount of the active ingredient compounds in such a formulation is 0.0001 to 95 mass%.
  • another active compound such as a pest control agent, a mite control agent, a nematode control agent, a disease control agent, a repellent, or a synergist
  • the compound of the present invention represented by the formula (1) can also be present together with another active compound as a mixing agent.
  • another active compound as a mixing agent.
  • the range of the objective pests to be controlled can be expanded by using the compound as a mixture with a compound (insecticide) having a pest-controlling activity, a tick-controlling activity, or a nematode-controlling activity, and synergistic effects, such as a reduction in dosage, can be expected.
  • an active compound include the followings.
  • Organophosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, daizinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, piridafenthion, profenofos, prothiofos, propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, and vamidothion;
  • the compound of the present invention represented by the formula (1) can also be present as a mixed agent with an active compound other than the compound having a pest-controlling activity, a tick-controlling activity, or a nematode-controlling activity.
  • an active compound other than the compound having a pest-controlling activity, a tick-controlling activity, or a nematode-controlling activity In order to control diseases and/or weeds that simultaneously occur in the time of use, a synergistic effect of a reduction in pest control labor and a reduction in dosage can be expected by using the compound of the present invention in combination with a compound having a bactericidal activity, an herbicidal activity, or a plant growth regulating activity. In addition, a more effective control effect by the synergistic effect, etc. can be expected by using the compound mixed with a repellent or a synergist.
  • Such an active compound examples include disease control agents, for example,
  • Examples of the compound having an herbicidal activity include
  • repellent examples include capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, and thiram.
  • synergist examples include methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonil butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, and verbutin.
  • the compound of the present invention is expected to provide the same effect as that of a biotic pesticide by being used in combination with the biotic pesticide, for example, a viral formulation, such as Cytoplasmic polyhedrosis virus (CPV), Entomopox virus (EPV), Granulosis virus (GV), or Nuclear polyhedrosis virus (NPV); a microbial pesticide that is used as an insecticide or a nematicide, such as Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, or Verticillium lecanii; a microbial pesticide that is used as a fungicide, such as Agrobacterium radiobactor, Bacillus subtilis, nonpathogenic Erwinia caroto
  • the present compound as a biotic pesticide in combination with, for example, a natural enemy, such as Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis, Hemiptarsenus varicornis, Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Phytoseiulus persimilis, Pilophorus typicus, or Piocoris varius; or a pheromone formulation, such as codlelure, cuelure, geraniol, g
  • 3-Chloroperbenzoic acid (0.27 g) was added to a solution of N-(methoxymethyl)-N- ⁇ 4-(trifluoromethyl)phenyl ⁇ -3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (0.22 g) in chloroform (3 mL), followed by stirring at room temperature for 4 hours. Saturated sodium bicarbonate water was added to the reaction solution, followed by extraction with chloroform. The resulting organic layer was washed with saturated saline solution and was then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the solvent was distilled under reduced pressure.
  • Formulations containing the compound of the present invention will now be specifically described with reference to some formulation examples, but the compound of the present invention, auxiliary ingredients, and the amounts thereof are not limited to those in the following Formulation Examples.
  • the term "part(s)" in the following Formulation Examples means part(s) by mass.
  • the compound (10 parts) of the present invention xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), and Sorpol 3005X (the trade name of a mixture of a nonionic surfactant and an anionic surfactant available from TOHO Chemical Industry Co., Ltd.) (10 parts) were uniformly mixed and dissolved to obtain an emulsion agent.
  • Nipsil NS-K (the trade name of white carbon available from Tosoh Silica Corporation) (10 parts), Kaolin Clay (the trade name of kaolinite available from Takehara Kagaku Kogyo Co., Ltd.) (60 parts), SAN X P-252 (the trade name of sodium lignin sulfonate available from NIPPON PAPER Chemicals Co., Ltd.) (5 parts), and Runox P-65L (the trade name of alkyl allyl sulfonate available from TOHO Chemical Industry Co., Ltd.) (5 parts) were uniformly mixed and pulverized in an air mill to obtain a water dispersible powder.
  • Nipsil NS-K the trade name of white carbon available from Tosoh Silica Corporation
  • Kaolin Clay the trade name of kaolinite available from Takehara Kagaku Kogyo Co., Ltd.
  • SAN X P-252 the trade name of sodium lignin sulfonate available from NIPPON PAPER Chemicals Co.,
  • Nipsil NS-K the trade name of white carbon available from Tosoh Silica Corporation (20 parts), Kaolin Clay (50 parts), Runox 1000C (the trade name of a naphthalene sulfonate condensate available from TOHO Chemical Industry Co., Ltd.) (5 parts), and Sorpol 5276 (the trade name of a nonionic surfactant available from TOHO Chemical Industry Co., Ltd.) (5 parts) were uniformly mixed and pulverized in an air mill to obtain a water dispersible powder.
  • Nipsil NS-K the trade name of white carbon available from Tosoh Silica Corporation
  • Kaolin Clay 50 parts
  • Runox 1000C the trade name of a naphthalene sulfonate condensate available from TOHO Chemical Industry Co., Ltd.
  • Sorpol 5276 the trade name of a nonionic surfactant available from TOHO Chemical Industry Co., Ltd.
  • the compound (20 parts) of the present invention Runox P-65L (the trade name of alkyl allyl sulfonate available from TOHO Chemical Industry Co., Ltd.) (3 parts), and a water-soluble carrier (potassium chloride) (77 parts) were uniformly mixed and pulverized to obtain a watersoluble agent.
  • Runox P-65L the trade name of alkyl allyl sulfonate available from TOHO Chemical Industry Co., Ltd.
  • a water-soluble carrier potassium chloride
  • Newkalgen BX-C (the trade name of sodium alkylnaphthalenesulfonate manufactured by TAKEMOTO OIL & FAT Co., Ltd.)
  • silicon dioxide (2 parts
  • a water-soluble carrier 43 parts
  • the compound (20 parts) of the present invention was dispersed in a mixed solution prepared in advance by mixing propylene glycol (5 parts), Sorpol 7933 (the trade name of an anionic surfactant available from TOHO Chemical Industry Co., Ltd.) (5 parts), and water (50 parts) to obtain a slurry-like mixture, this slurry-like mixture was then wet-pulverized with DYNO-MILL (Shinmaru Enterprise Corporation), and a dispersion prepared in advance by thoroughly mixing xanthan gum (0.2 parts) with water (19.8 parts) was added to the mixture to obtain a flowable agent.
  • DYNO-MILL Shinmaru Enterprise Corporation
  • Newkalgen FS-26 (the trade name of a mixture of dioctyl sulfosuccinate and polyoxyethylene tristyrylphenyl ether available from TAKEMOTO OIL & FAT Co., Ltd.) (5 parts), propylene glycol (8 parts), and water (50 parts) were mixed in advance, and this slurry-like mixture was wet-pulverized with DYNO-MILL (Shinmaru Enterprise Corporation). Subsequently, xanthan gum (0.2 parts) was thoroughly mixed with and dispersed in water (16.8 parts) to produce a gel-like substance and was sufficiently mixed with the pulverized slurry to obtain a flowable agent.
  • Newkalgen FS-26 the trade name of a mixture of dioctyl sulfosuccinate and polyoxyethylene tristyrylphenyl ether available from TAKEMOTO OIL & FAT Co., Ltd.
  • propylene glycol (8 parts)
  • water 50 parts
  • An antifoam agent Antifoam E-20 (the trade name of emulsion-type modified silicone available from Kao Corporation) (0.1 parts) was added to the resulting dispersion, and xanthan gum (0.2 parts) dispersed in propylene glycol (5.0 parts) was added thereto to obtain an emulsion (phase inversion emulsification).
  • the compound (10 parts) of the present invention was dissolved in xylene (10 parts) and was mixed with a surfactant Rheodol 430V (the trade name of polyoxyethylene sorbitol tetraoleate available from Kao Corporation) (24 parts).
  • a surfactant Rheodol 430V the trade name of polyoxyethylene sorbitol tetraoleate available from Kao Corporation
  • the resulting mixed solution, an antifoam agent Antifoam E-20 (the trade name of an emulsion-type modified silicone system available from Kao Corporation) (0.1 parts)
  • a preservative Proxel GX-L 0.1 parts
  • the compound (0.01 parts) of the present invention and Sorpol CA-42 (the trade name of a nonionic surfactant available from TOHO Chemical Industry Co., Ltd.) (0.1 parts) were mixed to be uniform, and water (99.79 parts) was then gradually added thereto with stirring. A preservative Proxel GX-L (0.1 parts) was added to the resulting dispersion to obtain a microemulsion.
  • Newkalgen D-945 the trade name of polyoxyethylene (20 moles) sorbitan monooleate available from TAKEMOTO OIL & FAT Co., Ltd.
  • 20 parts were mixed to be uniform, and water (69.9 parts) was then gradually added thereto with stirring.
  • a preservative Proxel GX-L (0.1 parts) was added to the resulting dispersion to obtain a microemulsion.
  • the compound (0.01 parts) of the present invention was dissolved in a solvent SOLVESSO 200 (0.08 parts) and Newkalgen ST-30 (the trade name of a mixture of polyoxyethylene arylphenyl ether formaldehyde condensate, a polyoxyalkylene arylphenyl ether, an alkylbenzene sulfonate, and xylene available from TAKEMOTO OIL & FAT Co., Ltd.) (0.12 parts) to be uniform, and water (99.69 parts) was gradually added thereto with stirring.
  • a preservative Proxel GX-L (0.1 parts) was added to the resulting dispersion to obtain a microemulsion.
  • the compound (5 parts) of the present invention, bentonite (30 parts), clay (60 parts), and sodium lignin sulfonate (5 parts) were uniformly mixed and pulverized, and water was added thereto, followed by thoroughly kneading. Then, extruding granulation and drying and sizing were performed to obtain granules.
  • Silica sand (90 parts) was put in an oscillating granulator and was hydrated, and the compound (5 parts) of the present invention, sodium lignin sulfonate (4 parts), polyvinyl alcohol (PVA) (0.5 parts), and white carbon (0.5 parts) that were mixed and pulverized in advance were then put in the granulator for coating. Drying and sizing were then performed to obtain granules.
  • Ishikawalite (89 parts) was put in an oscillating granulator and was hydrated, and the compound (5 parts) of the present invention, sodium lignin sulfonate (3 parts), sodium dioctyl sulfosuccinate (0.5 parts), POE styrylphenyl ether (2 parts), and polyvinyl alcohol (PVA) (0.5 parts) that were mixed and pulverized in advance were then put in the granulator for coating. Drying and sizing were then performed to obtain granules.
  • sodium lignin sulfonate 3 parts
  • sodium dioctyl sulfosuccinate 0.5 parts
  • POE styrylphenyl ether 2 parts
  • PVA polyvinyl alcohol
  • the compound (2 parts) of the present invention was diluted with a solvent and was mixed with pumice (98 parts) as a bulking agent by spraying the diluted solution.
  • the resulting granular composition was dried, followed by sieving to obtain fine granules.
  • the compound (5 parts) of the present invention was air milled or mechanochemically ground as needed.
  • This powdery source material and silica sand (85 parts) as a bulking agent were uniformly mixed, and the mixture was then mixed with a binder Toxanone GR-31A (10 parts) diluted with a solvent by spraying the diluted binder.
  • the resulting granular composition was dried, followed by sieving to obtain fine granules.
  • the compound (5 parts) of the present invention was uniformly mixed with white carbon (5 parts) and Clay (trade name, Nippon Talc Co., Ltd.) (90 parts), followed by pulverization to obtain a powder formulation.
  • the compound (5 parts) of the present invention was uniformly mixed with propylene glycol (0.5 parts) and DL Clay (94.5 parts), followed by pulverization to obtain a powder formulation.
  • the compound (10 parts) of the present invention, sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part), and Clay (trade name, Nippon Talc Co., Ltd.) (83 parts) were uniformly mixed and pulverized to prepare a powder formulation.
  • the powder formulation was mixed with pre-moistened seeds, followed by air drying to obtain coated seeds.
  • the insecticidal rate was 100%.
  • the insecticidal rates of Compound A and Compound B were 90% and 50%, respectively.
  • Test Example 2 Larvicide test for Spodoptera litura (Fabricius)
  • a water diluted solution of an emulsion agent (500 ppm) prepared as in Formulation Example 1 was put in a 120-mL polyethylene cup, and artificial feed Insecta LF (Nosan Corporation, diameter: 5 cm) sliced into 5 mm thickness and cut into 1/4 was immersed in the polyethylene cup for about 60 seconds. After the immersion treatment, the resultant artificial feed piece was put in another 120-mL polyethylene cup (diameter: 8 cm, height: 4 cm) with filter paper (diameter: 55 mm) on the bottom together with test insects, and the cup was covered with a lid and was then kept in a thermostat chamber of 25°C.
  • an emulsion agent 500 ppm
  • the insecticidal rate was 100%.
  • the insecticidal rates of Compound A and Compound B were 90% and 0%, respectively.
  • Test Example 3 Adult-killing test for Aculops lycopersici Massee
  • a lid provided with a hole (diameter: about 5 mm) at the center was put on a 430-mL polyethylene cup containing water.
  • Circular filter paper with a diameter of 6.5 cm which was cut such that a strip-shaped filter paper piece having a width of about 5 mm was formed was put on the lid, and the filter paper piece was inserted into the hole of the lid so that the tip of the piece extends downward from the hole and immersed in the water in the cup.
  • absorbent cotton was put on the filter paper such that the water in the cup was always supplied to the absorbent cotton.
  • Control rate A ⁇ 100 + B ⁇ 80 + C ⁇ 50 / A + B + C + D A: the number of disks for 100, B: the number for disks of 80, C: the number for disks of 50, D: the number of disks for 0.

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EP20822844.5A 2019-06-13 2020-06-12 Agent chimique agricole et horticole dont l'ingrédient actif est un nouveau dérivé d'imidazopyridine-2-carboxamide Pending EP3985004A4 (fr)

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MX2021015020A (es) 2022-01-18
AU2020290268A2 (en) 2022-03-03
KR20220024013A (ko) 2022-03-03
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BR112021024535A2 (pt) 2022-01-18
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